DE3722796A1 - Verfahren zum herstellen von 2,6-dihydroxynaphthalin - Google Patents
Verfahren zum herstellen von 2,6-dihydroxynaphthalinInfo
- Publication number
- DE3722796A1 DE3722796A1 DE19873722796 DE3722796A DE3722796A1 DE 3722796 A1 DE3722796 A1 DE 3722796A1 DE 19873722796 DE19873722796 DE 19873722796 DE 3722796 A DE3722796 A DE 3722796A DE 3722796 A1 DE3722796 A1 DE 3722796A1
- Authority
- DE
- Germany
- Prior art keywords
- naphthalene
- hydroxy
- propyl
- dihydroxynaphthalene
- amount
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 51
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 14
- DXIUSVDANCIIAR-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)naphthalen-2-yl]propan-2-ol Chemical compound C1=C(C(C)(C)O)C=CC2=CC(C(C)(O)C)=CC=C21 DXIUSVDANCIIAR-UHFFFAOYSA-N 0.000 claims abstract description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 27
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 12
- 229920000728 polyester Polymers 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 description 17
- 229960002163 hydrogen peroxide Drugs 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- -1 2-hydroxy-2-propyl Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000106 Liquid crystal polymer Polymers 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- GWLLTEXUIOFAFE-UHFFFAOYSA-N 2,6-diisopropylnaphthalene Chemical compound C1=C(C(C)C)C=CC2=CC(C(C)C)=CC=C21 GWLLTEXUIOFAFE-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- NPMYFXQHWHOQRO-UHFFFAOYSA-N 1-propylcyclohexa-2,4-dien-1-ol Chemical compound CCCC1(O)CC=CC=C1 NPMYFXQHWHOQRO-UHFFFAOYSA-N 0.000 description 1
- XREODDNQGGBCEW-UHFFFAOYSA-N 2,6-di(propan-2-yl)naphthalene hydrogen peroxide Chemical compound OO.OO.C1=C(C(C)C)C=CC2=CC(C(C)C)=CC=C21 XREODDNQGGBCEW-UHFFFAOYSA-N 0.000 description 1
- LEARFTRDZQQTDN-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C(C(C)(C)O)C=C1 LEARFTRDZQQTDN-UHFFFAOYSA-N 0.000 description 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000010543 cumene process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ZPWQALCOMQRMRK-UHFFFAOYSA-M sodium;6-hydroxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=CC2=CC(O)=CC=C21 ZPWQALCOMQRMRK-UHFFFAOYSA-M 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61166080A JPS6322532A (ja) | 1986-07-15 | 1986-07-15 | ２，６−ナフタレンジオ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3722796A1 true DE3722796A1 (de) | 1988-01-28 |
| DE3722796C2 DE3722796C2 (en, 2012) | 1989-07-27 |
Family
ID=15824608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873722796 Granted DE3722796A1 (de) | 1986-07-15 | 1987-07-10 | Verfahren zum herstellen von 2,6-dihydroxynaphthalin |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6322532A (en, 2012) |
| CA (1) | CA1271492A (en, 2012) |
| DE (1) | DE3722796A1 (en, 2012) |
| FR (1) | FR2601671B1 (en, 2012) |
| GB (1) | GB2192632B (en, 2012) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3618643A1 (de) * | 1985-06-07 | 1986-12-11 | Kureha Kagaku Kogyo K.K., Tokio/Tokyo | Verfahren zum herstellen von 2,6-naphthalindiol, und 2,6 diacetoxynaphthalin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3681026D1 (de) * | 1985-09-20 | 1991-09-26 | Mitsui Petrochemical Ind | Oxidierungsverfahren von 2,6-diisopropylnaphthalin. |
-
1986
- 1986-07-15 JP JP61166080A patent/JPS6322532A/ja active Granted
-
1987
- 1987-07-10 DE DE19873722796 patent/DE3722796A1/de active Granted
- 1987-07-14 GB GB8716572A patent/GB2192632B/en not_active Expired - Fee Related
- 1987-07-14 CA CA000542065A patent/CA1271492A/en not_active Expired - Fee Related
- 1987-07-15 FR FR878709939A patent/FR2601671B1/fr not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3618643A1 (de) * | 1985-06-07 | 1986-12-11 | Kureha Kagaku Kogyo K.K., Tokio/Tokyo | Verfahren zum herstellen von 2,6-naphthalindiol, und 2,6 diacetoxynaphthalin |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2192632B (en) | 1990-07-18 |
| GB2192632A (en) | 1988-01-20 |
| FR2601671B1 (fr) | 1990-05-11 |
| JPS6322532A (ja) | 1988-01-30 |
| CA1271492A (en) | 1990-07-10 |
| JPH0317813B2 (en, 2012) | 1991-03-11 |
| FR2601671A1 (fr) | 1988-01-22 |
| DE3722796C2 (en, 2012) | 1989-07-27 |
| GB8716572D0 (en) | 1987-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |